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Statements

Subject Item
n2:RIV%2F60461373%3A22810%2F11%3A43892807%21RIV12-MSM-22810___
rdf:type
n7:Vysledek skos:Concept
dcterms:description
Five flavin (isoalloxazine) and alloxazine adducts with O-nucleophiles, 5-ethyl-4a-hydroxy-3,7,8,10-tetramethyl-4a,5-dihydroisoalloxazine (1a-OH), 5-ethyl-4a-hydroxy-3,10-dimethyl-4a,5-dihydroisoalloxazine (1b-OH), 5-ethyl-4a-methoxy-3,10-dimethyl-4a,5-dihydroisoalloxazine (1b-OMe), 5-ethyl-4a-hydroxy-1,3-dimethyl-4a,5-dihydroalloxazine (2a-OH) and 5-ethyl-4a-methoxy-1,3-dimethyl-4a,5-dihydroalloxazine (2a-OMe) were prepared from the corresponding salts, 5-ethyl-3,7,8,10-tetramethylisoalloxazinium (la), 5-ethyl-3,10-dimethylisoalloxazinium (1b) and 5-ethyl-1,3-dimethylalloxazinium (2a) perchlorates by the addition of a nucleophile (water or methanol) and triethylamine as a base. The prepared adducts represent artificial analogs of Flavin cofactor derivatives which are essential for the functioning of flavoenzymes. They were characterized by (1)H and (13)C NMR, HR-MS and UV-VIS spectra. In the cases of la-OH, 1b-OH, and 2a-OMe, the crystal structures were determined by X-ray diffraction. Flavinium and alloxazinium salts are in rapid equilibria with their adducts in water or methanolic solutions without the presence of a base. It was found that the equilibrium constants for flavin adduct formation is higher by six orders of magnitude than those for alloxazine derivatives. The presence of the sp(3) hybridized C4a atom in the molecule of the adducts causes deviation from planarity. The inter-planar angles between benzene and the pyrimidine ring were found to be 31.5 degrees, 23.64 degrees and 15.62 degrees for 1a-OH, 1b-OH and 2a-OMe, respectively, which are much higher than those of previously published adducts of C-nucleophiles. In isoalloxazine adducts, delocalization of pi electrons between the N10-C10a and C10a-N1 bonds was detected while the length of the N10-C10a and C10a-N1 bonds in the alloxazine adducts corresponds to a double and single bond, respectively. Five flavin (isoalloxazine) and alloxazine adducts with O-nucleophiles, 5-ethyl-4a-hydroxy-3,7,8,10-tetramethyl-4a,5-dihydroisoalloxazine (1a-OH), 5-ethyl-4a-hydroxy-3,10-dimethyl-4a,5-dihydroisoalloxazine (1b-OH), 5-ethyl-4a-methoxy-3,10-dimethyl-4a,5-dihydroisoalloxazine (1b-OMe), 5-ethyl-4a-hydroxy-1,3-dimethyl-4a,5-dihydroalloxazine (2a-OH) and 5-ethyl-4a-methoxy-1,3-dimethyl-4a,5-dihydroalloxazine (2a-OMe) were prepared from the corresponding salts, 5-ethyl-3,7,8,10-tetramethylisoalloxazinium (la), 5-ethyl-3,10-dimethylisoalloxazinium (1b) and 5-ethyl-1,3-dimethylalloxazinium (2a) perchlorates by the addition of a nucleophile (water or methanol) and triethylamine as a base. The prepared adducts represent artificial analogs of Flavin cofactor derivatives which are essential for the functioning of flavoenzymes. They were characterized by (1)H and (13)C NMR, HR-MS and UV-VIS spectra. In the cases of la-OH, 1b-OH, and 2a-OMe, the crystal structures were determined by X-ray diffraction. Flavinium and alloxazinium salts are in rapid equilibria with their adducts in water or methanolic solutions without the presence of a base. It was found that the equilibrium constants for flavin adduct formation is higher by six orders of magnitude than those for alloxazine derivatives. The presence of the sp(3) hybridized C4a atom in the molecule of the adducts causes deviation from planarity. The inter-planar angles between benzene and the pyrimidine ring were found to be 31.5 degrees, 23.64 degrees and 15.62 degrees for 1a-OH, 1b-OH and 2a-OMe, respectively, which are much higher than those of previously published adducts of C-nucleophiles. In isoalloxazine adducts, delocalization of pi electrons between the N10-C10a and C10a-N1 bonds was detected while the length of the N10-C10a and C10a-N1 bonds in the alloxazine adducts corresponds to a double and single bond, respectively.
dcterms:title
Synthesis and structural studies of flavin and alloxazine adducts with O-nucleophiles Synthesis and structural studies of flavin and alloxazine adducts with O-nucleophiles
skos:prefLabel
Synthesis and structural studies of flavin and alloxazine adducts with O-nucleophiles Synthesis and structural studies of flavin and alloxazine adducts with O-nucleophiles
skos:notation
RIV/60461373:22810/11:43892807!RIV12-MSM-22810___
n7:predkladatel
n8:orjk%3A22810
n3:aktivita
n12:Z n12:P
n3:aktivity
P(GA203/07/1246), Z(AV0Z40550506), Z(MSM6046137302)
n3:cisloPeriodika
1-3
n3:dodaniDat
n9:2012
n3:domaciTvurceVysledku
n20:7241852
n3:druhVysledku
n14:J
n3:duvernostUdaju
n5:S
n3:entitaPredkladatele
n16:predkladatel
n3:idSjednocenehoVysledku
233887
n3:idVysledku
RIV/60461373:22810/11:43892807
n3:jazykVysledku
n17:eng
n3:klicovaSlova
SULFIDES; SALTS; OXYGEN; AMINES; H2O2 OXIDATIONS; ELECTRON-TRANSFER; CRYSTAL-STRUCTURES; MOLECULAR-STRUCTURE; HYDROGEN-PEROXIDE; MONOAMINE-OXIDASE CATALYSIS
n3:klicoveSlovo
n10:OXYGEN n10:SULFIDES n10:MOLECULAR-STRUCTURE n10:MONOAMINE-OXIDASE%20CATALYSIS n10:AMINES n10:H2O2%20OXIDATIONS n10:HYDROGEN-PEROXIDE n10:CRYSTAL-STRUCTURES n10:SALTS n10:ELECTRON-TRANSFER
n3:kodStatuVydavatele
NL - Nizozemsko
n3:kontrolniKodProRIV
[7C8D95DEBFE6]
n3:nazevZdroje
Journal of Molecular Structure
n3:obor
n4:CC
n3:pocetDomacichTvurcuVysledku
1
n3:pocetTvurcuVysledku
6
n3:projekt
n21:GA203%2F07%2F1246
n3:rokUplatneniVysledku
n9:2011
n3:svazekPeriodika
1004
n3:tvurceVysledku
Eigner, Václav Šanda, Miloslav Čejka, Jan Ménová, Petra Dvořáková, Hana Cibulka, Radek
n3:wos
000296927300024
n3:zamer
n11:MSM6046137302 n11:AV0Z40550506
s:issn
0022-2860
s:numberOfPages
10
n15:doi
10.1016/j.molstruc.2011.08.002
n13:organizacniJednotka
22810